


A Thousand Miles

by thescroller



Category: Supernatural
Genre: F/M
Language: English
Status: In-Progress
Published: 2019-10-10
Updated: 2020-02-17
Packaged: 2020-11-28 17:49:04
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,274
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20970569
Author URL: https://archiveofourown.org/users/thescroller/pseuds/thescroller
Summary: A business trip with your boss Dean Smith, the man you’ve been drooling over since your first day, a delayed flight and some choice words. What could possibly go wrong?





	1. Un;

** Part One **

Working at Sandover Bridge & Iron Inc. had one, and honestly, only one, perk to it.

Well, the health benefits and 401k were nice touches, but that was something that the adult in you appreciated. Other than that, the place was a hot mess at all times, one time you heard there were mentions of some kid in IT trying to convince others that the vacant floor above your office was haunted. It was proof that enough time there and it would turn your brain into mush. This was why in your downtime, you had been scrounging through job listings online, waiting for the day that one of the several office assistant jobs would hurry up and get back to you.

No, what was the only perk was the man strutting in through the main doors like he owned the place; Dean Smith.

Pouty, plump lips pursed in thought at all times, freckles that looked like they had been individually kissed on by an angel of the Lord themselves and green eyes that carried such intensity, you were surprised he hadn’t burned a hole through the smartphone he was almost always glued to. Some of the other office ladies said he was God’s gift to them, but little did they know - that man was the bane of your existence these days.

But, you’d be damned if the view of him wasn’t worth it; most days.

Typically the office staff went scrambling when they heard his car pull into the parking lot, trying to make themselves look as busy as possible and today was no exception.

You stood up from your spot at the corner desk, closest to the wide window and world that still existed outside and tried to remind yourself that you only had a couple more hours before you could kiss this place goodbye for the better part of seventy-two hours. Dean walked in, the BlueTooth clipped to his ear as he nodded his head in silent agreement to the voice on the other end.

“Yeah, yeah, completely,” he said, as the sea of people separated in his presence while his eyes searched the crowd. When they landed on where you were always so patiently waiting, he jutted his chin in the direction of his closed office door. “You’ll see me there.”

Waiting until he was just past the corner of your desk, you turned on your heel and followed him into the clean, crisp space that was known as his office. Taking your spot on one of the overly stuffed leather chairs across from where he was standing behind his desk, you waited until he was ready to give you your tasks for the day ahead.

“Alright, sounds good.”

There was no closure, just another quick nod and Dean clicked the side of his wireless device before taking a deep breath, adjusting a couple of stacks of papers on his desk and turning his attention back to where you were being the good little lap dog.

“Morning Mister Smith,” you said, almost robotically as you gripped the little stack of notes in your hand. “I have a couple of messages for you.”

“Go on.”

You brushed some of your stray hairs out of your face as you tried not to focus on how great your boss looked in his suit today. “Susan from accounting needed to speak with you about one of the client accounts not pushing through, but I was told you needed to check your email with that regard. Then, Mr. Wesson in IT wanted to let you know that your printer should be up and running again.”

“Why wasn’t the damn thing working last night?”

Stifling the laugh that was bubbling up at the remembrance of the pure exasperation on Sam Wesson’s face when he had strolled out late yesterday, you gave the simple answer. “It just needed to be turned off and then back on again.”

Mister Smith had been walking over to his personal coffee maker when he halted, only briefly, before giving a shake of his head. You didn’t need to be facing him to know that he was embarrassed. “Oh.”

You smirked quietly to yourself as you read off the last and most important of the messages, “Mr. Alder called again, something about one of his accounts faltering.”

There was a sharp inhale as he focused on making his cup of coffee just right before he spoke again, “I just got off the phone with him.”

Clicking your pen, you flipped open to an empty sheet on your notepad, “What do I need to do?”

Usually, Dean Smith was quick to quip off a laundry list of things that needed to be done. If it was anything to get him to the top, possibly CEO of the company, he was all about it, but this morning, he was unusually quiet. You didn’t know what was worse, the sudden silence coming from the back of him or the massive list of things that needed to be done before the day was over.

“Mister Smith?” You tried, thinking maybe his BlueTooth had rung and he picked up without you noticing, which with the clock ticking in the back of your mind about your break, it was very possible.

His shoulders squared as he turned to face you, his eyes cast downwards to the spinning swirl of his black coffee. “I need to head to Toronto, meet with this client and solidify our contract.”

“Okay,” you nodded. “So you want me to look into a hotel and book a flight for you?”

“Just for one night. It’ll actually need to be two rooms in the hotel.”

Something wasn’t sitting right all of the sudden. Maybe it was his lack of intense eye contact or how his tone was coming off… a little more hushed than usual, but the whole conversation was suddenly causing your stomach to twist. Keeping your eyes on the blank pad before you, you asked your question slowly. “Oh? Are you meeting the client there?”

“Well, no.”

Your next approach was a little more cheeky than you usually were with the man. “Got a hot date?”

It was hard to not miss the little side smirk from him as he ran a hand down the front of his face, his eyes crinkling in the corners before turning their jade stare towards your expectation frame. He noticed that for the first time all week, you took a little extra time to get yourself ready, the pencil skirt hugging your thighs in an exceptional way this morning while you actually had your hair loose, falling down the length of your back whereas you usually had it up in a tight bun to allow easy errand running without having to eat half of it in the process.

“It’s actually for you.”

You opened your mouth, but nothing came out for a solid twenty seconds. Finally, you found the question hiding in the back of your throat. “Excuse me?”

There was a deep breath, the kind of breath that was usually followed with the last thing you wanted to hear. “Alder asked me to finish this deal in person, tomorrow morning before coming back before Friday.”

“And how exactly do I tie into this equation?”

“I need the best girl there with me.”

Your usual professional demeanor was thrown out the window as you stood up, sizing up the large man across from you. His relaxed lean against the counter had you thinking about all the possible ways you could quit and still get that Christmas bonus you had been promised months ago. “I think you’re confusing me with Jessica. I have no experience in sales.”

“That’s not why I need you there.”

Again, you stared at Dean unable to ask the correct questions. You were honestly at a loss for words as you tried to figure out if the man was trying to pull some sort of practical joke, something to kick off the brief closure the company would be having for the holidays - something that hadn’t happened in basically forever.

Taking your silence and your glare as the go-ahead to explain some more, Mister Smith finally pushed himself up and made his way back towards his desk. “See,” usually, you’d sit back down, but the nerves jumping around in your gut were forcing you to remain standing, “You're the only one who knows my schedule like the back of my hand, you know all the big accounts and the numbers. You know all the people who will say ‘yes’ in a heartbeat.”

“That can all be put into a memo.”

He shook his head. “That’s not good enough. I need you there. I need to have everything within my reach to guarantee that I close this deal.”

“Sir,” you cleared your throat. “I have plans to fly out and see my family this weekend.”

“Y/N, please, this is a requirement.”

“I’m just an assistant.”

His eyes were no longer on you as he settled himself into his desk, the facade of Dean Smith coming into all of his finely chiseled features. “This is a requirement, you either come with me or don’t bother coming back to work on Monday.”

With tears pricking at the corners of your eyes, you gave your boss a silent nod and made your way back out towards your secluded desk, but not before Leigh caught your eye. The redhead offered you a wide smile only for you to give her a shake of your head and sink down into the thin computer chair. You continued to wrap your head around what you were expected to do, weighing the pros and cons to saying ‘fuck it’ and giving this place the massive middle finger before boarding your plane back to Ohio.

Your decision still flip-flopped while you absently reached for the desk phone, dialing the numbers that you had memorized since you were six years old. The line rang three times before a comforting familiar voice wandered through. “How’s my favorite girl?”

“Hey Dad,” you sighed, the emotions already starting to crack through your words. “Is mom free?”

“Sure thing sugar plum,” he bounced back, the smile ever-present in his tone while there was a dial shuffle of what could only be your father’s shirt pressed against the cordless phone as he went on the hunt for your mother - who, after looking at the clock, was probably starting to get the stuffing ready for Christmas dinner.

There was a mumble of words, nothing you could make out until another familiar question echoed through. “What’s wrong?”

“Well, hello to you too Mom.”

“You’re my daughter,” you heard her put something down and imagined her settling into one of the many dining room chairs before speaking again. “I always know when something is wrong.”

Silent tears threatened to spill over as you tried to find the courage to tell your mother that you wouldn’t be home for the holiday… again. “I have to go to Canada.”

“Okay.”

“Okay?” You asked, turning your chair around so that you were staring at the blank white wall behind you. “You’re not going to say anything else.”

There was a soft sigh on the other end. “Honey, I know you’re a hard worker. It would have been great to have you home for Christmas this year, but you need to make something of yourself out there.”

“Oh, yeah, being an office assistant is totally getting myself out there.”

Your mother laughed, cracking a bit at the end allowing you to know that she as just as upset about your news, but doing her damnedest to keep it to herself. “Once you publish that book of yours, you’ll be rolling in the money.”

Those pesky tears were back again, only this time they freely flowed at the utter support your parents gave you about pursuing your dreams, even when it meant overworking at one job to support the one you’d always wanted.

An idea popped into your head as you crossed and uncrossed your legs once more. “I’ll be on the first flight on Saturday. I just want to see you guys for a full twenty-four hours.”

“Just let me know when we need to come and get you.”

You swiped at your cheeks now, sitting up a little taller - your mother’s unwavering support strong in your veins. “I love you.”

“To the moon and back Little One.”

Hanging up, you opened up your computer, pulling up the airline sight that you always had to go through for business trips while quickly clicking on the first-class seats. Even if you had to be stuck with the office hardass, you might as well make sure your own was treated to all the plush seating available.

Dean Smith wasn’t going to bring you down.

\--- 


	2. Deux;

**Part Two**

Since you had been the one to book the tickets, you made sure to seat yourself as far away as possible from your boss. Even though you knew you were only there to play fetch for the man, you could at least pretend like you were jetting off to some lavish vacation until after the meeting. You were counting down the hours until you were able to hop back on to the plane and put all these stresses behind you for the better part of twenty-four hours. 

As predicted, you were completely useless to the two businessmen across from you. Mr. Smith was his usual witty and charming self, getting a solid couple of laughs out of the other man while slyly throwing in a couple of bits of business conversation. While you still thought of your boss as an ass and a half, you couldn’t deny that the man was damn good at his job. An even smaller part of you wondered how that charm would work on the ladies in his life.

Despite knowing way more than you should about your boss, considering you wrote his calendar out for him and one time he even asked you to call and cancel his date with some woman named Lisa, you still couldn’t help the way your stomach did a little jolt when he turned a smirk over to you. 

“So what do you say?” He asked, sliding his gaze from you back to the stout balding man across from him. “Do we have a deal?” 

There was a moment of silence while you watched the man think through his options. While Sandover did have higher pricing, there was no denying the added benefit of great customer service - even the IT guys were damn good at their jobs. Come on, even you just being here with Dean was proof enough that the company went above and beyond for their clients - even if overworked several of their employees.

It was common knowledge that they just looked at the numbers over anything. 

As the seconds ticked by, you watched as the client released a slow breath of air before standing up quickly, a smile enveloping his tired features while he stuck out a hand to Mr. Smith. “Just show me the dotted line.” 

It was only another hour and a half before you were practically skipping your way through the halls of the building, your carry-on tossed over your shoulder and per usual, Dean was glued to his phone while typing out the details of his meeting to his superiors. You paid no mind to what he was doing, instead focusing on flagging the shuttle down that would get the two of you to the airport and get you on the next flight home. 

“Jesus woman,” you heard him mutter behind you, but you chose not to give him the satisfaction of an answer when a large white van pulled up before you. “This isn’t a marathon.” 

Rolling your eyes, you stepped up through the large space and pushed yourself up against the window, the chill of the glass seeping through your light sweater and used your bag as a barrier between you and the large man coming up behind you. Once the two of you were settled, you turned your focus towards the landscape ahead of you. Montreal was a beautiful city. If you hadn’t been here for a business trip, you would have probably ached to find a way to admire the place, but right now all you had on your mind was your mother’s world-famous pecan pie. 

“Too bad we couldn’t sightsee,” Dean spoke quietly as if reading your mind. “I’m sure some poutine would be amazing right now.” 

Unable to help yourself, you turned towards him with a raised eyebrow, the unasked question poised on your lips before the driver cut in. “You all heading to the airport?” 

“Yes,” the two of you answered in unison. 

There was a sort of grumble that followed the man as he turned on his blinker to get into the on-coming traffic. “I hope you have some backup plans.”

Dread settled itself into the pit of your stomach while you tried to catch the driver’s gaze in the rearview mirror. “Why?”

“There’s a storm coming.” 

That dread spread it’s way up to your chest, gripping you tightly. “I’m sure we’ll miss it.” 

With a click of his tongue, he remained silent confirming your worst fear. Thankfully, Mr. Smith stayed quiet next to you, but you felt the way he kept stealing glances at you as you tried to will Mother Nature to bend her knee when the first of many snow flurries started dancing down from the sky. 

“Fuck,” you whispered. 

\--- 

_**CANCELED**_. 

The word mocked your very existence as you glared at the neon signage.

There was no denying the disappointment you were feeling as you dragged behind Dean now. You didn’t know if you could face calling your parents and giving them the news. The clerks had assured you that there was a good chance the storm was just going to run through the night and, God willing, you could be out on the first flight in the morning.

For once, you were grateful that Dean always had his phone glued to his palm because he was quick to look up nearby hotels. Due to the weather, the two of you decided to just trudge the short distance to shelter instead of trying to get comfortable at the airport in the hopes the all-clear would come sooner. Apparently you guys weren’t the only ones with the idea to get a room for the night because the moment you stepped into the well-lit lounge, you were greeted with the hustle and bustle of an unexpected change of plans. 

You stole a glance at your boss, only to find him with his phone pressed to his ear and a nod in your direction. He didn’t need to tell you what to do as you pushed your way through the small gathering of people towards the front desk where three employees were clearly doing their best to keep it together. 

Offering the younger woman closer to you a sympathetic smile, you cleared your throat. “Uh, hi, I’m looking for two rooms for the night.” 

She gave a quick nod, turning her attention towards the computer in front of her, her fingers flying over the keyboard. You watched as her eyes squinted at the screen before she looked back up at you. “So we have a room,” she started. “But just one room.” 

As if your day couldn’t get any worse. 

“One?” 

Now it was her turn to return the look you had given her moments ago. “With the impending storm and several flights being halted, we filled up pretty quickly.”

You sighed telling her to just go ahead and book it, handing over the expense card you always kept on hand in case Mr. Smith asked you to do some ridiculous errands at the last second. When all was said and done, you waded your way through the crowd once more, the room card in hand feeling like it weighed as much as a gold brick. As you came back into his line of sight, Dean looked up from where he was leaning against the wall, his face falling at the clear defeat written all across your face. As you stepped closer, you made the mental note to never try your hand at poker because you clearly couldn’t bluff to save your life. 

“Do we need to hunt down a different hotel?” He asked quickly, shoulder’s sagging while he adjusted the computer bag hanging off of him. “Maybe I can call around and see what we can get.”

You wanted to lie and tell him to find another place, but another part of you just wanted to sit at a bar and drown your sorrows in a bottle or two. “While that probably would have been great thinking before we got here,” you held up the card toward him with a stiff smirk, “we got a room.” 

“Oh, good,” he sighed before his gaze hardened. “Wait. A room?” 

You stayed silent while he put two and two together. He glanced around at the little circles of people in the shared space, seeming to understand what had happened. “Do you know what kind of room?”

“Just a standard room.” 

He nodded, adjusting his bag once more and reaching over for the card to inspect the room number like it was of the utmost importance. “So I assume there is a couch?”

“Uh, yeah, I guess so.”

“Hm.” 

Now you stared at him as he turned on his heel towards where the elevator was and began the short walk over before quickly followed in his steps. Just as he pushed the button, allowing it to light up, you spoke your question. “Why do you care if there is a couch?” 

There was a ding as the steel box appeared on the main floor, sliding the door open to let it’s occupants out and leaving just you and Mr. Smith to the soft elevator music that followed. He leaned against the wall to his right, allowing himself to look over at where you were focusing on the rising numbers. “So that I know I have a place to sleep.” 

“Or we can just keep checking to see if there is another room available…” 

Your boss shook his head, mouth twitching like he was trying to fight back a smile. “Too late.”

The doors slid open and Dean held out an arm for you to go ahead of him. This whole situation was leaving you with a slight panic building in your chest. “It might not be too late,” you babbled, glancing down the hall to where your shared room awaited. “Maybe we’ll get really lucky and they’ll just find a room that no one is in!” 

There was a chuckle from behind you, but you avoided the glance back. “C’mon Y/N, it’ll be fine. This way we can still make sure we are on the same flight and hold each other accountable.” 

Room 315 came into view and you paused. “Accountable? You mean I really am here just to be your babysitter?”

The playful grin he had been toying with had completely disappeared now as he realized just how bad his suggestion sounded. “What? No, no.” 

You raised your eyebrow but stayed silent when you crossed your arms. 

“I just mean,” his tongue clicked as he turned his focus to the slot in front of the two of you, slipping the thin card in with ease until there was a beep. “I could really use a drink.”

“Okay?” 

Was he reading your mind?

He didn’t say another word as he pushed the door open and flipping on the closest light switch, bathing the whole room in a yellow glow. It wasn’t anything special, a queen-sized bed sat in the middle of the room with a tiny couch and coffee table tucked in the corner with a desk and a coffee maker in place. The bathroom was immediately to your left and as you took the five steps to get into the cozy space, you considered whether or not you wanted to shower and just crawl into bed, but the anxiety of this trip was getting the better of you. 

“You know,” you started as you plopped your bag at the foot of the bed. “I think drinking should be a business expense today.” 

There was a low laugh from Dean. “In this condition, booze is absolutely a business expense.” 

You knew you couldn’t hide the look of surprise written across your face by the way that Dean looked at you with amusement in those green eyes of his. It almost was like he was messing with you just to see the kind of reaction it would get. Where was this Dean Smith at the office? 

“Yeah?” You half-heartedly asked, finding yourself slightly embarrassed at how long you had been staring at the way his eyes crinkled up in the corners.

He gave you a soft nod. “Let’s ditch the work and get some drinks, maybe a little dinner.” 

“If I didn’t know any better I’d say this sounds like a date.” 

Just as quickly as you said those words did you clamp your mouth shut and feel your cheeks flush with heat. The twinkle in his eyes was unmistakable, but thankfully the man had the good sense to keep his thoughts to himself. You were certain if he said anything about the little outburst, you would just combust.

That smirk still teasing his lips, he turned his head towards the door with a slight nod. “Ready to go then?” 

\----


End file.
